ES2245339T3 - Polimeros y copolimeros de dienos con un grupo alcoxisilano. - Google Patents
Polimeros y copolimeros de dienos con un grupo alcoxisilano.Info
- Publication number
- ES2245339T3 ES2245339T3 ES01130207T ES01130207T ES2245339T3 ES 2245339 T3 ES2245339 T3 ES 2245339T3 ES 01130207 T ES01130207 T ES 01130207T ES 01130207 T ES01130207 T ES 01130207T ES 2245339 T3 ES2245339 T3 ES 2245339T3
- Authority
- ES
- Spain
- Prior art keywords
- epoxycyclohexyl
- group
- glycidoxypropyl
- delm
- polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 106
- 229920001577 copolymer Polymers 0.000 title claims abstract description 42
- -1 aromatic vinyl hydrocarbon Chemical class 0.000 claims abstract description 51
- 125000000524 functional group Chemical group 0.000 claims abstract description 48
- 150000001993 dienes Chemical class 0.000 claims abstract description 37
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 28
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 28
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 28
- 239000000178 monomer Substances 0.000 claims abstract description 27
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 21
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 13
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 12
- 239000003999 initiator Substances 0.000 claims abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 229910000077 silane Inorganic materials 0.000 claims abstract description 10
- 125000004429 atom Chemical group 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 25
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 20
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 12
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 12
- 125000003700 epoxy group Chemical group 0.000 claims description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
- FBNXYLDLGARYKQ-UHFFFAOYSA-N methoxy-dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(C)CCCOCC1CO1 FBNXYLDLGARYKQ-UHFFFAOYSA-N 0.000 claims description 4
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 claims description 4
- ORDZXCQDZLMHAM-UHFFFAOYSA-N 2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl-triphenoxysilane Chemical compound C1CC2OC2CC1CC[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 ORDZXCQDZLMHAM-UHFFFAOYSA-N 0.000 claims description 3
- ROYZOPPLNMOKCU-UHFFFAOYSA-N 2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl-tripropoxysilane Chemical compound C1C(CC[Si](OCCC)(OCCC)OCCC)CCC2OC21 ROYZOPPLNMOKCU-UHFFFAOYSA-N 0.000 claims description 3
- LUHNDPHGSUCBBP-UHFFFAOYSA-N bis[3-(oxiran-2-ylmethoxy)propyl]-diphenoxysilane Chemical compound C1OC1COCCC[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)CCCOCC1CO1 LUHNDPHGSUCBBP-UHFFFAOYSA-N 0.000 claims description 3
- DJWNEZWBDQYOHO-UHFFFAOYSA-N bis[3-(oxiran-2-ylmethoxy)propyl]-dipropoxysilane Chemical compound C1OC1COCCC[Si](OCCC)(OCCC)CCCOCC1CO1 DJWNEZWBDQYOHO-UHFFFAOYSA-N 0.000 claims description 3
- QXFPLBCPMHBSAQ-UHFFFAOYSA-N butoxy-methyl-bis[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C1OC1COCCC[Si](C)(OCCCC)CCCOCC1CO1 QXFPLBCPMHBSAQ-UHFFFAOYSA-N 0.000 claims description 3
- XHHFICKLGBTSLY-UHFFFAOYSA-N dibutoxy-methyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](C)(OCCCC)OCCCC)CCC2OC21 XHHFICKLGBTSLY-UHFFFAOYSA-N 0.000 claims description 3
- CHBHIAULMYNWBG-UHFFFAOYSA-N diethoxy-ethyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](CC)(OCC)OCC)CCC2OC21 CHBHIAULMYNWBG-UHFFFAOYSA-N 0.000 claims description 3
- ASGKDLGXPOIMTM-UHFFFAOYSA-N diethoxy-methyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](C)(OCC)OCC)CCC2OC21 ASGKDLGXPOIMTM-UHFFFAOYSA-N 0.000 claims description 3
- LKZLQNPMYAFYFM-UHFFFAOYSA-N diethyl-methoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](CC)(CC)OC)CCC2OC21 LKZLQNPMYAFYFM-UHFFFAOYSA-N 0.000 claims description 3
- XZXYTQWKUONLLI-UHFFFAOYSA-N dimethoxy-bis[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C1OC1COCCC[Si](OC)(OC)CCCOCC1CO1 XZXYTQWKUONLLI-UHFFFAOYSA-N 0.000 claims description 3
- SLQTWNAJXFHMHM-UHFFFAOYSA-N dimethoxy-methyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](C)(OC)OC)CCC2OC21 SLQTWNAJXFHMHM-UHFFFAOYSA-N 0.000 claims description 3
- SEHVKHDGLSELEV-UHFFFAOYSA-N dimethyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]-phenoxysilane Chemical compound C1CC2OC2CC1CC[Si](C)(C)OC1=CC=CC=C1 SEHVKHDGLSELEV-UHFFFAOYSA-N 0.000 claims description 3
- HROVXMRQCKFDTL-UHFFFAOYSA-N ethyl-dimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](CC)(OC)OC)CCC2OC21 HROVXMRQCKFDTL-UHFFFAOYSA-N 0.000 claims description 3
- ZGQPRKMIRUWRBS-UHFFFAOYSA-N ethyl-dimethyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)butoxy]silane Chemical compound C1C(C(CO[Si](C)(C)CC)CC)CCC2OC21 ZGQPRKMIRUWRBS-UHFFFAOYSA-N 0.000 claims description 3
- OPZRKYKXKJAZPL-UHFFFAOYSA-N ethyl-dimethyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethoxy]silane Chemical compound C1C(CCO[Si](C)(C)CC)CCC2OC21 OPZRKYKXKJAZPL-UHFFFAOYSA-N 0.000 claims description 3
- JRVJEOIFFSNVTG-UHFFFAOYSA-N ethyl-dimethyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)propoxy]silane Chemical compound C1C(C(C)CO[Si](C)(C)CC)CCC2OC21 JRVJEOIFFSNVTG-UHFFFAOYSA-N 0.000 claims description 3
- 239000012634 fragment Substances 0.000 claims description 3
- YKSZBBZEHPPESP-UHFFFAOYSA-N methoxy-dimethyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](C)(C)OC)CCC2OC21 YKSZBBZEHPPESP-UHFFFAOYSA-N 0.000 claims description 3
- KWALCKUJBZXIJB-UHFFFAOYSA-N methoxy-tris[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C1OC1COCCC[Si](CCCOCC1OC1)(OC)CCCOCC1CO1 KWALCKUJBZXIJB-UHFFFAOYSA-N 0.000 claims description 3
- RKNLZBHCYFVPCH-UHFFFAOYSA-N methyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]-bis(prop-1-en-2-yloxy)silane Chemical compound C1C(CC[Si](C)(OC(=C)C)OC(C)=C)CCC2OC21 RKNLZBHCYFVPCH-UHFFFAOYSA-N 0.000 claims description 3
- CMVRXZWIGKJZKG-UHFFFAOYSA-N methyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]-diphenoxysilane Chemical compound C1CC2OC2CC1CC[Si](C)(OC=1C=CC=CC=1)OC1=CC=CC=C1 CMVRXZWIGKJZKG-UHFFFAOYSA-N 0.000 claims description 3
- VLKBRFNUOVSNJA-UHFFFAOYSA-N methyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]-dipropoxysilane Chemical compound C1C(CC[Si](C)(OCCC)OCCC)CCC2OC21 VLKBRFNUOVSNJA-UHFFFAOYSA-N 0.000 claims description 3
- UEQFSKQXQPIFDJ-UHFFFAOYSA-N methyl-bis[3-(oxiran-2-ylmethoxy)propyl]-phenoxysilane Chemical compound C1OC1COCCC[Si](OC=1C=CC=CC=1)(C)CCCOCC1CO1 UEQFSKQXQPIFDJ-UHFFFAOYSA-N 0.000 claims description 3
- ZNMFUUQNAZADMP-UHFFFAOYSA-N methyl-bis[3-(oxiran-2-ylmethoxy)propyl]-propoxysilane Chemical compound C1OC1COCCC[Si](C)(OCCC)CCCOCC1CO1 ZNMFUUQNAZADMP-UHFFFAOYSA-N 0.000 claims description 3
- OAVPBWLGJVKEGZ-UHFFFAOYSA-N tributoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCCCC)(OCCCC)OCCCC)CCC2OC21 OAVPBWLGJVKEGZ-UHFFFAOYSA-N 0.000 claims description 3
- FQYWWLSIKWDAEC-UHFFFAOYSA-N tributoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCOCC1CO1 FQYWWLSIKWDAEC-UHFFFAOYSA-N 0.000 claims description 3
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 claims description 3
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 claims description 3
- ZQMPLYWXYJXIGG-UHFFFAOYSA-N triethyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethoxy]silane Chemical compound C1C(CCO[Si](CC)(CC)CC)CCC2OC21 ZQMPLYWXYJXIGG-UHFFFAOYSA-N 0.000 claims description 3
- LQZHZFUSFHLGHE-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(C(C)C[Si](OC)(OC)OC)CCC2OC21 LQZHZFUSFHLGHE-UHFFFAOYSA-N 0.000 claims description 3
- DAJFVZRDKCROQC-UHFFFAOYSA-N 3-(oxiran-2-ylmethoxy)propyl-tripropoxysilane Chemical compound CCCO[Si](OCCC)(OCCC)CCCOCC1CO1 DAJFVZRDKCROQC-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- ZTNCUEXCRLSMLI-UHFFFAOYSA-N dibutoxy-bis[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C1OC1COCCC[Si](OCCCC)(OCCCC)CCCOCC1CO1 ZTNCUEXCRLSMLI-UHFFFAOYSA-N 0.000 claims description 2
- JIOUJECYOVQAMA-UHFFFAOYSA-N dibutoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCCCO[Si](C)(OCCCC)CCCOCC1CO1 JIOUJECYOVQAMA-UHFFFAOYSA-N 0.000 claims description 2
- RIIYEOHOQDANAR-UHFFFAOYSA-N diethoxy-bis[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C1OC1COCCC[Si](OCC)(OCC)CCCOCC1CO1 RIIYEOHOQDANAR-UHFFFAOYSA-N 0.000 claims description 2
- ODADONMDNZJQMW-UHFFFAOYSA-N diethoxy-ethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](CC)(OCC)CCCOCC1CO1 ODADONMDNZJQMW-UHFFFAOYSA-N 0.000 claims description 2
- WZJMRIMGNYUTSE-UHFFFAOYSA-N ethoxy-diethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](CC)(CC)CCCOCC1CO1 WZJMRIMGNYUTSE-UHFFFAOYSA-N 0.000 claims description 2
- YQAUYOHZPMSXLV-UHFFFAOYSA-N ethoxy-methyl-bis[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C1OC1COCCC[Si](C)(OCC)CCCOCC1CO1 YQAUYOHZPMSXLV-UHFFFAOYSA-N 0.000 claims description 2
- YYDBOMXUCPLLSK-UHFFFAOYSA-N ethyl-dimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CC[Si](OC)(OC)CCCOCC1CO1 YYDBOMXUCPLLSK-UHFFFAOYSA-N 0.000 claims description 2
- NEULXKNYWZBFDH-UHFFFAOYSA-N methoxy-methyl-bis[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound C1OC1COCCC[Si](C)(OC)CCCOCC1CO1 NEULXKNYWZBFDH-UHFFFAOYSA-N 0.000 claims description 2
- ICCDZMWNLNRHGP-UHFFFAOYSA-N methyl-[3-(oxiran-2-ylmethoxy)propyl]-bis(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](C)(OC(C)=C)CCCOCC1CO1 ICCDZMWNLNRHGP-UHFFFAOYSA-N 0.000 claims description 2
- CUIXFHFVVWQXSW-UHFFFAOYSA-N methyl-[3-(oxiran-2-ylmethoxy)propyl]-diphenoxysilane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(C)CCCOCC1CO1 CUIXFHFVVWQXSW-UHFFFAOYSA-N 0.000 claims description 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 claims description 2
- ZQPNGHDNBNMPON-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CO[Si](OC)(OC)CCC(C)OCC1CO1 ZQPNGHDNBNMPON-UHFFFAOYSA-N 0.000 claims description 2
- 229920005604 random copolymer Polymers 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 5
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 67
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 48
- 229920001971 elastomer Polymers 0.000 description 42
- 239000005060 rubber Substances 0.000 description 40
- 239000000377 silicon dioxide Substances 0.000 description 18
- 238000005299 abrasion Methods 0.000 description 17
- 239000000463 material Substances 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 12
- 238000009826 distribution Methods 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000005056 compaction Methods 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000005062 Polybutadiene Substances 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 229920002857 polybutadiene Polymers 0.000 description 7
- 230000002787 reinforcement Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 230000006872 improvement Effects 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 239000010734 process oil Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 5
- 229910052792 caesium Inorganic materials 0.000 description 5
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 229910052701 rubidium Inorganic materials 0.000 description 5
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000004073 vulcanization Methods 0.000 description 5
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 4
- 244000043261 Hevea brasiliensis Species 0.000 description 4
- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 229920003052 natural elastomer Polymers 0.000 description 4
- 229920001194 natural rubber Polymers 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920005555 halobutyl Polymers 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 description 1
- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
- CKVWBMJEETWJTF-UHFFFAOYSA-N lithium;tributyltin Chemical compound CCCC[Sn]([Li])(CCCC)CCCC CKVWBMJEETWJTF-UHFFFAOYSA-N 0.000 description 1
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 1
- 239000002370 magnesium bicarbonate Substances 0.000 description 1
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 description 1
- 235000014824 magnesium bicarbonate Nutrition 0.000 description 1
- VOARQMXRPHXHID-UHFFFAOYSA-N methyl-[3-(oxiran-2-ylmethoxy)propyl]-dipropoxysilane Chemical compound CCCO[Si](C)(OCCC)CCCOCC1CO1 VOARQMXRPHXHID-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- RBCYCMNKVQPXDR-UHFFFAOYSA-N phenoxysilane Chemical group [SiH3]OC1=CC=CC=C1 RBCYCMNKVQPXDR-UHFFFAOYSA-N 0.000 description 1
- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- KKFOMYPMTJLQGA-UHFFFAOYSA-N tribenzyl phosphite Chemical compound C=1C=CC=CC=1COP(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 KKFOMYPMTJLQGA-UHFFFAOYSA-N 0.000 description 1
- FPBXRRDHCADTAL-UHFFFAOYSA-N triethoxy(3-nitropropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC[N+]([O-])=O FPBXRRDHCADTAL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- QPPXVBLDIDEHBA-UHFFFAOYSA-N trimethoxy(3-nitropropyl)silane Chemical compound CO[Si](OC)(OC)CCC[N+]([O-])=O QPPXVBLDIDEHBA-UHFFFAOYSA-N 0.000 description 1
- QUTZUATVZPXUJR-UHFFFAOYSA-N trinonyl phosphite Chemical compound CCCCCCCCCOP(OCCCCCCCCC)OCCCCCCCCC QUTZUATVZPXUJR-UHFFFAOYSA-N 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L19/00—Compositions of rubbers not provided for in groups C08L7/00 - C08L17/00
- C08L19/006—Rubber characterised by functional groups, e.g. telechelic diene polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Graft Or Block Polymers (AREA)
- Tires In General (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35239093 | 1993-12-29 | ||
| JP35238993 | 1993-12-29 | ||
| JP35238993 | 1993-12-29 | ||
| JP35239093 | 1993-12-29 | ||
| JP15754094A JP3514824B2 (ja) | 1993-12-29 | 1994-07-08 | 重合体及びその重合体組成物 |
| JP15754094 | 1994-07-08 | ||
| JP30385294 | 1994-12-07 | ||
| JP30385294A JP3441201B2 (ja) | 1993-12-29 | 1994-12-07 | 重合体及びその重合体組成物 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2245339T3 true ES2245339T3 (es) | 2006-01-01 |
Family
ID=27473487
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES01130207T Expired - Lifetime ES2245339T3 (es) | 1993-12-29 | 1994-12-29 | Polimeros y copolimeros de dienos con un grupo alcoxisilano. |
| ES97100466T Expired - Lifetime ES2179965T3 (es) | 1993-12-29 | 1994-12-29 | Polimeros y copolimeros de dieno que tienen un grupo de alcoxisilano. |
| ES94120914T Expired - Lifetime ES2128500T3 (es) | 1993-12-29 | 1994-12-29 | Polimeros y copolimeros dienicos con un grupo alcoxisilano. |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES97100466T Expired - Lifetime ES2179965T3 (es) | 1993-12-29 | 1994-12-29 | Polimeros y copolimeros de dieno que tienen un grupo de alcoxisilano. |
| ES94120914T Expired - Lifetime ES2128500T3 (es) | 1993-12-29 | 1994-12-29 | Polimeros y copolimeros dienicos con un grupo alcoxisilano. |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5508333A (fr) |
| EP (3) | EP1199313B1 (fr) |
| DE (3) | DE69430958T2 (fr) |
| ES (3) | ES2245339T3 (fr) |
Families Citing this family (105)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0987426A (ja) * | 1995-09-20 | 1997-03-31 | Bridgestone Corp | ゴム組成物の製造方法 |
| DE69622235T2 (de) * | 1995-10-04 | 2003-01-23 | Compagnie Generale Des Etablissements Michelin-Michelin & Cie., Clermont-Ferrand | Kautschukmischung basierend auf einem Dienpolymer mit von Organosilanen abgeleiteten Gruppen zur Verwendung in Reifenlaufflächen |
| JP3736580B2 (ja) * | 1996-02-23 | 2006-01-18 | 日本ゼオン株式会社 | ジエン系ゴム |
| JP2954878B2 (ja) * | 1996-06-11 | 1999-09-27 | ニチアス株式会社 | フロン及び／又は冷凍機油用のゴム組成物と加硫シール部品 |
| JP3685572B2 (ja) * | 1996-12-17 | 2005-08-17 | 住友ゴム工業株式会社 | タイヤトレッド用ゴム組成物 |
| US6252007B1 (en) | 1997-07-11 | 2001-06-26 | Bridgestone Corporation | Elastomers having a reduced hysteresis via interaction of polymer with silica surfaces |
| US5872176A (en) | 1997-07-11 | 1999-02-16 | Bridgestone Corporation | Addition of salts to improve the interaction of silica with rubber |
| US6525118B2 (en) | 1997-07-11 | 2003-02-25 | Bridgestone Corporation | Processability of silica-filled rubber stocks with reduced hysteresis |
| US5916961A (en) * | 1997-07-11 | 1999-06-29 | Bridgestone Corporation | Amine-initiated elastomers having hysteresis reducing interaction with silica |
| US5866650A (en) * | 1997-07-11 | 1999-02-02 | Bridgestone Corporation | Composition of cyclic amine-initiated elastomers and amorphous silica and process for the production thereof |
| US6221943B1 (en) | 1997-07-11 | 2001-04-24 | Bridgestone Corporation | Processability of silica-filled rubber stocks |
| US6384117B1 (en) | 1997-07-11 | 2002-05-07 | Bridgestone Corporation | Processability of silica-filled rubber stocks |
| US6369138B2 (en) | 1997-07-11 | 2002-04-09 | Bridgestone Corporation | Processability of silica-filled rubber stocks with reduced hysteresis |
| US6344538B1 (en) | 1998-08-24 | 2002-02-05 | Iowa State University Research Foundation, Inc. | Functionalized diene monomers and polymers containing functionalized dienes and methods for their preparation |
| US6100373A (en) * | 1998-08-24 | 2000-08-08 | Iowa State University Research Foundation, Inc. | Functionalized diene monomers and polymers containing functionalized dienes and methods for their preparation |
| ES2234193T3 (es) | 1998-10-07 | 2005-06-16 | Jsr Corporation | Caucho extendido con aceite y composicion de caucho. |
| EP1018521A1 (fr) | 1999-01-06 | 2000-07-12 | Société de Technologie Michelin | Procede de preparation de polymeres dieniques fonctionnalises amine, de tels polymeres, composition de caoutchouc et enveloppe de pneumatique comportant ces polymeres. |
| EP1208142A1 (fr) * | 1999-04-22 | 2002-05-29 | Dunlop Tire Corporation | Compositions elastomeres vulcanisables utilisees comme bandes de roulement |
| US6852785B1 (en) * | 1999-04-22 | 2005-02-08 | Dunlop Tire Corporation | Vulcanizable elastomeric compositions for use as tire treads |
| WO2001034658A1 (fr) * | 1999-11-12 | 2001-05-17 | Bridgestone Corporation | Polymeres modifies produits a l'aide de catalyseurs a base de lanthanides |
| US6977281B1 (en) * | 1999-11-12 | 2005-12-20 | Bridgestone Corporation | Modified polymers prepared with lanthanide-based catalysts |
| US6279632B1 (en) | 1999-11-24 | 2001-08-28 | Bridgestone Corporation | Method to control increase in viscosity during aging of siloxane modified polymers |
| WO2001075738A1 (fr) * | 2000-03-31 | 2001-10-11 | Front End Capital, Llc | Levee de capitaux pour societes naissantes par l'intermediaire d'un cabinet de courtage |
| US6573412B1 (en) | 2000-05-12 | 2003-06-03 | Bridgestone Corporation | Chain-coupled polymeric alkoxide compounds having controlled viscosity |
| US6313210B1 (en) | 2000-07-31 | 2001-11-06 | Bridgestone Coporation | Silica-reinforced rubber compounds containing moisture stabilized polymers |
| WO2002038615A1 (fr) | 2000-11-10 | 2002-05-16 | Bridgestone Corporation | Cis-1,4-polybutadiene eleve fonctionalise prepare au moyen de nouveaux agents de fonctionnalisation |
| JP2002201310A (ja) * | 2000-12-27 | 2002-07-19 | Bridgestone Corp | ゴム組成物 |
| CN100347208C (zh) * | 2001-09-27 | 2007-11-07 | Jsr株式会社 | 共轭二烯均聚或共聚橡胶、均聚或共聚橡胶的制造方法、橡胶组合物、复合体以及轮胎 |
| US6806307B2 (en) * | 2001-10-11 | 2004-10-19 | Bridgestone Corporation | Synthesis and use of chain-coupled polymeric sulfide compounds in rubber formulations |
| EP1319673A1 (fr) * | 2001-12-12 | 2003-06-18 | Bayer Ag | Polymères modifiés par des groupes fonctionnalisés |
| JP4744144B2 (ja) * | 2002-08-30 | 2011-08-10 | 株式会社ブリヂストン | 官能性ポリマー、及びそれにより改良された加硫物 |
| WO2004111094A1 (fr) | 2003-06-09 | 2004-12-23 | Bridgestone Corporation | Compositions elastomeres presentant une hysteresis amelioree et comprenant des polymeres a terminaison sequentielle |
| TWI385182B (zh) * | 2004-03-15 | 2013-02-11 | Jsr Corp | Conjugated diene (co) poly rubber and method for producing the same |
| US9034962B2 (en) * | 2004-04-27 | 2015-05-19 | Bridgestone Corporation | Method of producing a tire composition having improved silica reinforcement |
| US20080295935A1 (en) * | 2004-08-10 | 2008-12-04 | Jsr Corporation | Rubber Composition and Tire |
| BRPI0516818B1 (pt) * | 2004-10-02 | 2017-06-13 | Firestone Polymers, Llc | Composition of modified asphalt, asphalt concrete, copolymer in dibloco and its preparation process |
| US7335411B2 (en) * | 2004-10-26 | 2008-02-26 | Bridgestone Corporation | Method of producing a tire composition having improved silica reinforcement |
| US7836928B2 (en) * | 2004-10-26 | 2010-11-23 | Bridgestone Corporation | Method of producing a tire composition having improved silica reinforcement |
| JP5226217B2 (ja) * | 2004-11-10 | 2013-07-03 | 株式会社カネカ | 硬化性組成物 |
| WO2006076670A2 (fr) * | 2005-01-14 | 2006-07-20 | Bridgestone Corporation | Compositions de pneumatique et vulcanisats constitues de ces compositions presentant un renforcement en silice accru |
| US7879952B2 (en) * | 2005-12-28 | 2011-02-01 | Bridgestone Corporation | Functionalized polymers |
| US7671138B2 (en) * | 2006-05-26 | 2010-03-02 | Bridgestone Corporation | Polymers functionized with hydrobenzamides |
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| JP2007323544A (ja) * | 2006-06-05 | 2007-12-13 | Sony Corp | 情報処理システム、情報処理装置、および方法、並びにコンピュータ・プログラム |
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| US7732534B2 (en) * | 2006-08-28 | 2010-06-08 | Bridgestone Corporation | Polymers functionalized with nitro compounds |
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| ZA200711159B (en) * | 2006-12-28 | 2009-03-25 | Bridgestone Corp | Amine-containing alkoxysilyl-functionalized polymers |
| US7335706B1 (en) | 2007-03-05 | 2008-02-26 | The Goodyear Tire & Rubber Company | Method of making alkoxy functionalized rubbery polymers |
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| KR101707693B1 (ko) * | 2008-11-11 | 2017-02-16 | 트린세오 유럽 게엠베하 | 개질된 중합체의 제조시 실란올을 제거하는 방법 |
| US8188195B2 (en) | 2008-12-31 | 2012-05-29 | Bridgestone Corporation | Polymers functionalized with nitroso compounds |
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| JP5584288B2 (ja) | 2010-04-16 | 2014-09-03 | 旭化成ケミカルズ株式会社 | 変性共役ジエン系重合体の製造方法、及び変性共役ジエン系重合体組成物 |
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| FR3061187B1 (fr) | 2016-12-22 | 2019-02-01 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc avec une bonne dispersion de quantites elevees de charge inorganique renforcante |
| EP3626773B1 (fr) * | 2017-05-15 | 2021-12-08 | Bridgestone Corporation | Composition de caoutchouc pour pneu et pneu |
| EP3431511A1 (fr) * | 2017-07-19 | 2019-01-23 | ARLANXEO Deutschland GmbH | Caoutchouc diénique ramifié en étoile |
| US20210340306A1 (en) * | 2018-06-20 | 2021-11-04 | Bridgestone Corporation | High Strength Hydrogenated Polymers, And Rubber Compositions Incorporating Same |
| WO2021126624A1 (fr) * | 2019-12-17 | 2021-06-24 | Exxonmobil Chemical Patents Inc. | Additif pour bande de roulement à base de polymères fonctionnalisés pour améliorer le freinage sur chaussée humide et la résistance au roulement dans un pneu d'été à faible teneur en silice |
| EP4077528B1 (fr) | 2019-12-17 | 2024-09-18 | ExxonMobil Chemical Patents Inc. | Polymères fonctionnalisés en tant qu'additiv pour bande de roulement pour améliorer la performance des pneus toutes saisons |
| CN111116634A (zh) * | 2019-12-18 | 2020-05-08 | 怡维怡橡胶研究院有限公司 | 一种酰亚胺基封端巯基硅烷偶联剂及其合成方法和应用 |
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|---|---|---|---|---|
| US3764592A (en) * | 1970-06-29 | 1973-10-09 | Dow Corning | Silicon-polybutadiene resins |
| JPS525071A (en) * | 1975-07-01 | 1977-01-14 | Ooizumi Kojo:Kk | Improvement in machining of plummer block |
| GB1597500A (en) * | 1977-12-29 | 1981-09-09 | Shell Int Research | Polymers |
| JPS56104906A (en) * | 1980-01-25 | 1981-08-21 | Asahi Chem Ind Co Ltd | Polymer having reactive end group |
| JPS6250346A (ja) * | 1985-08-30 | 1987-03-05 | Bridgestone Corp | タイヤ用ゴム組成物 |
| JPH0651746B2 (ja) * | 1986-03-31 | 1994-07-06 | 日本合成ゴム株式会社 | シラン化合物変性重合体の製造方法 |
| US5006603A (en) * | 1986-09-26 | 1991-04-09 | Ube Industries, Ltd. | Fiber-reinforced rubber composition and production process and use thereof |
| JPH0713158B2 (ja) * | 1987-01-14 | 1995-02-15 | 株式会社ブリヂストン | タイヤ |
| US4935471A (en) * | 1987-10-15 | 1990-06-19 | The Goodyear Tire & Rubber Company | Capped polydienes |
| US5369175A (en) * | 1993-11-09 | 1994-11-29 | Shell Oil Company | Method for preparing asymmetric radial copolymers having four first arms and two second arms |
-
1994
- 1994-12-29 US US08/365,936 patent/US5508333A/en not_active Expired - Lifetime
- 1994-12-29 ES ES01130207T patent/ES2245339T3/es not_active Expired - Lifetime
- 1994-12-29 ES ES97100466T patent/ES2179965T3/es not_active Expired - Lifetime
- 1994-12-29 DE DE69430958T patent/DE69430958T2/de not_active Expired - Lifetime
- 1994-12-29 ES ES94120914T patent/ES2128500T3/es not_active Expired - Lifetime
- 1994-12-29 DE DE69434472T patent/DE69434472T2/de not_active Expired - Lifetime
- 1994-12-29 EP EP01130207A patent/EP1199313B1/fr not_active Expired - Lifetime
- 1994-12-29 EP EP97100466A patent/EP0773231B1/fr not_active Expired - Lifetime
- 1994-12-29 DE DE69417195T patent/DE69417195T2/de not_active Expired - Lifetime
- 1994-12-29 EP EP94120914A patent/EP0661298B1/fr not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0773231A3 (fr) | 1997-07-02 |
| EP0661298A3 (fr) | 1995-09-20 |
| DE69434472D1 (de) | 2005-09-29 |
| DE69434472T2 (de) | 2006-06-14 |
| EP0773231A2 (fr) | 1997-05-14 |
| US5508333A (en) | 1996-04-16 |
| EP1199313B1 (fr) | 2005-08-24 |
| EP1199313A3 (fr) | 2003-02-05 |
| DE69417195D1 (de) | 1999-04-22 |
| DE69430958T2 (de) | 2003-01-23 |
| EP0773231B1 (fr) | 2002-07-10 |
| ES2179965T3 (es) | 2003-02-01 |
| DE69417195T2 (de) | 1999-07-29 |
| DE69430958D1 (de) | 2002-08-14 |
| EP1199313A2 (fr) | 2002-04-24 |
| EP0661298B1 (fr) | 1999-03-17 |
| EP0661298A2 (fr) | 1995-07-05 |
| ES2128500T3 (es) | 1999-05-16 |
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